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18 Fun & Romantic Things to do in Milwaukee

Guide to fun things to do in Milwaukee for couples looking for unique things to do and cool date ideas

Milwaukee is a stunning Wisconsin city on the banks of Lake Michigan and couples from all over the world vacation here when they travel to Wisconsin.

The local people have responded by creating many romantic things to do in Milwaukee. A holiday with your partner is a truly special time, so you want to make sure that every moment is perfect.

I have put together this guide of romantic things to do in Wisconsin, WI, to make it easier to plan your adventure together. Read on to discover the best bars, cafes, and romantic Milwaukee activities.

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Overview: Top 5 Romantic Things to do in Milwaukee

  • Get a Couples Spa Treatment
  • Drink at a Rooftop Bar
  • Wander on the Riverwalk
  • Go for a Swan Paddle Boat Ride
  • Enjoy a Candlelit Dinner

1. Drink at a Rooftop Bar

most romantic things to do in Milwaukee, drink on table of rooftop bar at sunset with view over city

One of the most breathtaking characteristics of Milwaukee is its skyline, which lights up at night.

There are some truly romantic spots in Milwaukee where you can watch this skyline while enjoying a drink, but the trendy Historic Third Ward is the best place to go.

Here, you can find a few rooftop bar options where you can cuddle up under blankets next to fire pits and enjoy the amazing views.

Outsider Rooftop Bar is the locals’ favorite, with jaw-dropping panoramic views over much of the city and a sophisticated bar offering every cocktail you could dream of.

This is undoubtedly one of the best things to do in Milwaukee at night for couples.

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2. Enjoy a Candlelit Dinner

what to do in Milwaukee for couples, Two people having a candlelit dinner with one reaching romantically towards the face of the other over a couple of glasses of wine

You don’t have to go from Outsider Rooftop Bar to find one of the most romantic restaurants in Milwaukee.

Lux Domes at Benelux Café offers an unmatched experience where you can enjoy a private heated dome that is available all year.

Alongside two drinks of your choice, you can settle in for a high-end dining experience.

Renting a Lux Dome for the night is definitely one of the more expensive romantic things to do in Milwaukee.

However, this one-of-a-kind experience is well worth it to celebrate couples last night on Milwaukee romantic getaways.

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3. Go for a Swan Paddle Boat Ride

fun things to do in Milwaukee for couples, view of the legs of people standing on paddle boards in a calm body of water

While there are plenty of classy, romantic things to do in Milwaukee, some couples will be drawn to something more quirky.

One of the most unique and fun dates in Milwaukee is going for a swan paddle boat ride under the stars.

At certain times of the year, you can rent an LED-lit-up swan paddle boat in the lagoon at Veteran’s Park. Here, you can cuddle up and look at the night sky and the cityscape from below.

If you’re a couple who loves finding fun outdoor activities in Milwaukee, then this is a must. It is also a more affordable date idea, with renting costing around $30 per hour.

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4. Milwaukee River Boat Cruise

places to go on a date in Milwaukee, View of a large boat lit up with bright colorful lights as it sails down a wide river at nighttime

The best way to get to know Milwaukee is to go for a boat tour, where you can see the sights and learn about the city.

You will understand the city at a deeper level from a different perspective, and the tour guide should be able to tell you about all the romantic places in Milwaukee.

If you prefer more active and collaborative Milwaukee couples activities, then you should rent a kayak to paddle down the river together and at your own pace.

Make sure to keep an eye out for the Milwaukee Riverwalk and the Art Museum.

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5. Get a Taste of the City

romantic restaurants in Milwaukee, Close up shot of a pair of tacos filled with beans and cilantro with a couple of small dips to one side all sitting on a blue ceramic plate

Everyone loves to try different food and drinks when they go on holiday, and Milwaukee holds its own as a city with fantastic cheeses and breweries.

Amongst the best fun things to do in Milwaukee for couples is taking yourself for an adventure to try as many foods and drinks as possible.

There are lots of great independent shops, cafes, bars, and restaurants to explore. There are even many great vegan restaurants in Milwaukee to check out.

If you aren’t sure where to start, booking a walking tasting tour is one of the great things to do on a date in Milwaukee.

Taking a walk around the most historic parts of the city, the guide can introduce all the businesses that continue to influence Milwaukee cuisine, and there will be plenty of free samples to try.

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6. Enjoy a Movie at the Starry Avalon Theater

romantic places in Milwaukee, red theater seats getting blurry as the rows go back

The Starry Avalon Theatre is amongst the best places to go on a date in Milwaukee, which is especially worth doing in the winter as it is a chance to get cozy in the cold weather.

It’s one of my favorite things to do in Milwaukee in January to avoid the cold as you can catch all the big holiday releases without the crowds.

The theater has an unreal atmosphere with a star-covered ceiling that will make you feel like you are enjoying a movie under the stars.

This theater is also amongst the amazing Milwaukee attractions for couples with more discerning tastes because of the quality of films that are put on.

The lineup of films is carefully curated from a selection of classics and the latest releases.

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7. Wander on the Riverwalk

Milwaukee couples activities, Shot of large bridge over a river with the bright sun shining behind it on a mostly clear day

If the weather holds during your trip to the city, you will want to enjoy a romantic walk together, and wandering on the Riverwalk is among the most romantic things to do in Milwaukee.

Just make sure you wear grippy shoes, as the path may be icy.

This Milwaukee couples activity is more a cultural experience than a walk because of the tremendous sights to take in.

Alongside the beautiful skyline to gaze up at, there are some unmissable pieces of art. RiverSculpture is an outdoor gallery with a range of sculptures from local artists.

Meanwhile, the Bronze Fonz statue nearby pays homage to Arthur Fonzarelli, a character in the popular 70s sitcom Happy Days.

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8. Milwaukee Public Market

romantic spots in Milwaukee, street view of front of Milwaukee Public Market building with large neon sign on the roof on a bright clear day

There are plenty of romantic places to eat in Milwaukee, but few come with as much variety as the Milwaukee Public Market.

This bustling market runs all year and is packed to the rafters with artisan foods from throughout Wisconsin.

One of the best romantic things to do in Milwaukee, the market is perfect to visit in the winter because it is all covered.

There is no chance of getting rained or snowed on while you are trying exciting new foods with your partner.

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9. Red Arrow Park Ice Skating

romantic things to do in Milwaukee in winter, feet of someone ice skating on clear, thick ice

Like all cities, ice skating is one of the most popular romantic things to do in Milwaukee, and Red Arrow Park is the place to go.

This is an ice skating area even bigger than New York’s Rockefeller Center, open all winter. Skating is free if you own your own skates, or you can hire them.

Ice skating in winter is one of many great date ideas in Milwaukee because the area is transformed as Christmas approaches.

Fairy lights and decorations make the whole area incredibly beautiful and it’s easy to see why this is one of the top things to do in Milwaukee in winter.

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10. Milwaukee Art Museum

Romantic things to do in Milwaukee, WI, view of Milwaukee Art Museum with modern architecture comprised of many white beams and cable supports flanked by two steep verges of green grass under a clear azure blue sky

The Milwaukee Art Museum is another of the incredible things to do in Milwaukee for couples if you are fancying something more cultured.

Inside a unique building resembling a bird taking flight, you can explore a museum with 30,000 artworks, including paintings by Pablo Picasso and Andy Warhol.

Walking through this art gallery is a great way to spend a romantic afternoon because you can connect over the paintings that mean the most to you.

If you want a break, you can take a seat at the brilliant rooftop cafe, one of the best cafes in Milwaukee, which offers spectacular views over Lake Michigan and the city.

Milwaukee Art Museum is open Wednesday to Sunday and is an affordable date, costing just $22 for entry.

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11. Mitchell Park Domes

best outdoor Milwaukee activities for couples, peaceful botanical garden underneath a dome on a clear blue day

Whichever of the romantic things to do in Milwaukee, WI, you choose for a vacation in the winter, there is a risk that you might get cold.

This is not the case in the controlled environment of the Mitchell Park Horticultural Conservatory, which has a rich history since 1899.

Across three domes – Desert, Floral, and Tropical – you can find beautiful flora from around the world within a warm environment throughout.

These domes bring nature right into the heart of the city so you and your partner can get a break from the hustle and bustle.

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12. Tiki Love Bowls at At Random

fun things to do in Milwaukee for couples at night, Close up shot of two cocktails with fruit and many straws sitting on a bar in a club

Located on South Delaware Avenue, At Random is the best cocktail lounge in the city for couples.

It is one of the best fun things to do in Milwaukee for couples at night because of their famous Tiki Love Bowls.

These are massive and delicious cocktails that you can settle into with your partner for a whole evening.

At Random is a hugely romantic setting to share a drink, established in 1964. It has comfortable leather seating, vintage decor, and low, cozy lighting.

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13. Ride the Sky Glider

fun dates in Milwaukee, Aerial view of tall skyscrapers in various shapes sitting among areas of green grass with the coast and the sea visible behind

Milwaukee hosts a great range of festivals during the long and warm days of a Wisconsin summer at the Henry Mater Festival Grounds.

There are many to choose from, all playing some of the hottest bands and attracting visitors from all over the world, but the most popular is Summerfest.

These festivals are great for couples, but riding the Sky Glider is even more romantic. This is a ski lift that takes you from the festival grounds into the downtown skyline.

Hundreds of couples spend an evening riding it, watching the skyline and the vast crowds of festivalgoers as the sun sets.

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14. Stay at a Boutique Hotel

best Milwaukee romantic getaways, Woman sitting on a large grey sofa with a laptop in a hotel room next to a window

There are plenty of romantic hotels in Milwaukee to choose from, each offering high-end luxury service.

But, the most unique is the Saint Kate Arts Hotel, which features local art throughout the hotel, and every room has been curated based on a chosen art style.

You can also enjoy pop-up galleries and exhibitions, which will be different every time you visit.

There are a range of other boutique hotels spread across Milwaukee, including some of the most romantic hotels in Wisconsin.

For a quintessential and historic experience, you should choose County Clare or the Pfister.

Meanwhile, for a romantic experience that is more modern and urban, I suggest the Iron Horse or the Hotel Metro.

15. Live Music at the Blu Bar & Lounge

enjoy some of the best romantic things to do in Milwaukee, person wearing bowtie and waistcoat playing an acoustic guitar

Of all the romantic things to do in Milwaukee for couples, few offer the same incredible level of escapism as the Blu Bar & Lounge, which is located on the top floor of the Pfister.

This rooftop bar offers stunning views over the city with some of the finest cocktails in Wisconsin.

Something that keeps couples coming back to the Blu Bar & Lounge is the brilliant live music that you can catch there.

On Friday and Saturday nights, you can hear wonderful jazz music played live, usually based around the Pfister’s grand piano.

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16. Get a Couples Spa Treatment

looking for romantic things to do in Milwaukee, close up shot of three red towels neatly folded and placed on top of a white bed next to a soft white pillow with two delicate and decorative white and yellow flowers

Your romantic adventure to Wisconsin is all about relaxing in each other’s company, and where better to do this than at a spa?

The best place for a shared experience is the WELL Spa, located at the bottom of the Pfister, one of the top spa resorts in Wisconsin.

This excellent location offers a range of couples’ treatments, including the Doubles Relax Me package and the Doubles Deep Tissue and Yoga Balm package.

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17. Share Creativity at a Candle-Making Class

things to do in Milwaukee for couples, close up shot of a person's hand holding a lit match as they light up a scented candle

Scents like jasmine, lavender, blue lotus, and sandalwood have always been associated with romance, and you can fill your home with these smells by making a candle together to take back with you.

Glassnote Candle Bar runs a couples candle-making class where you can learn this unique skill while enjoying their great range of drinks.

It is the perfect way to create a beautiful reminder of your trip together.

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18. Remember the Trip with a Photography Session

Milwaukee anniversary ideas, old camera, film roll, negatives, and magnifying glass all laying on a dark wooden tabletop

There is no end to the unbelievable photo opportunities in Milwaukee looking out over the astonishingly beautiful Lake Michigan.

Thousands of visitors just use their phones to get snaps for their Instagram, but you can commemorate romantic getaways in Wisconsin by hiring a professional photographer.

Getting a professional photoshoot is one of the best Milwaukee anniversary ideas because it is the best way to get amazing photos.

They will be high quality, and your photographer will know all the most stunning spots. Photoshoots will also allow you to expand the romance beyond your trip.

You can form an even closer connection with your partner by choosing your favorite pictures together to be displayed in your home.

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Working out what to do in Milwaukee for couples should be easy because it is a great city to spend a vacation with your loved ones.

As the nights draw in this month, there are plenty of cozy, romantic things to do in Milwaukee in winter.

All of the options suggested in this list will work during the colder months, so make sure you use them when coming up with date ideas in Milwaukee.

FAQs About Romantic Things to do in Milwaukee

Where should I go on a date in Milwaukee to eat?

There are lots of great restaurants to choose from for date nights in Milwaukee but one of my favorites is Lux Domes at Benelux Café.

Is Milwaukee a romantic city?

Milwaukee is an incredibly romantic city and is arguably one of the most underrated romantic cities in the USA. There is so much to do here for couples, including popular romantic outings as well as more unique date ideas.

What are the best things to do in Milwaukee for couples?

There are a lot of amazing romantic things to do in Milwaukee. A few of my favorites are couples spa treatments, getting a drink on a rooftop bar and enjoying the view, walking along the river, paddle boarding, or taking a candlemaking course together.

Before You Go: Top Tips for your Trip 

Want more fun things to do in Milwaukee for couples? Check out our webstory.